


Grieving Jack

by alwaysthrowsscissors



Category: Supernatural
Genre: Anal Virgin Sam Winchester, Angst, Angst and Hurt/Comfort, Biting, Bottom Sam Winchester, Canon Compliant, Choking, Comfort Sex, Dean Winchester/Sam Winchester First Time Having Sex, Episode: s14e08 Byzantium, First Time, First Time Blow Jobs, First Time Bottoming, Grief/Mourning, Hurt Sam Winchester, Hurt/Comfort, M/M, Manhandling, One Shot, Pain, Plot What Plot/Porn Without Plot, Porn with Feelings, Rough Sex, Season/Series 14, Shameless Smut, Smut, Top Dean Winchester, Top Dean Winchester/Bottom Sam Winchester
Language: English
Status: Completed
Published: 2020-06-16
Updated: 2020-06-16
Packaged: 2021-03-04 04:34:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24747652
Author URL: https://archiveofourown.org/users/alwaysthrowsscissors/pseuds/alwaysthrowsscissors
Summary: Jack has died; his body could no longer withstand his lack of grace. Cas, Dean, and Sam mourn his loss but no one is taking it harder than Sam. Feeling guilted by Cas, Dean attempts to comfort his brother. This shameless fic is what may have happened if Dean didn't fall asleep at the kitchen table in S14e8.
Relationships: Dean Winchester/Sam Winchester
Comments: 13
Kudos: 161





	Grieving Jack

As Jack’s body lay in a room within the bunker, his three fathers began to drink; Dean drank to forget, Sam drank to soothe, and Castiel drank to belong. They laughed at fond memories of Jack’s childish innocence, and lamented the moments and experiences they would never have with him. Eventually, they fell into a pensive silence.

“I need to call it," Sam said wearily, getting up from the kitchen table, stumbling a bit against the door frame on his way out of the room.

Dean nodded as Castiel murmured “Goodnight, Sam.”

Castiel diverted his gaze to Dean reaching for the nearly empty bottle of whiskey. He pushed the bottle away from the human and gave him a significant look.

“Hey,” snapped Dean, “since when do you try to cut me off?”

“Your brother is suffering, Dean.”

“We're all suffering Cas.” He stood to snag the bottle away from the angel. “Like I said, he just needs space.”

“He just took off without telling us and broke down in the woods. He needs you right now," Castiel replied, maintaining his stern, blunt tone.

“I think I know, better than anyone, what my brother needs.” He poured the rest of the alcohol in his glass and downed it in one swallow, frowning at Castiel.

“When will you decide to look passed your own stubbornness and try to really see him?” Castiel’s piercing gaze did not waiver from Dean.

Dean sat silently looking defiant; he hated when Cas challenged him. He rotated the bottom ridge of his empty glass against the table, watching the last drop of brown liquid roll.

“Well?” Castiel prompted.

“Booze is all gone; time for bed," Dean said gruffly, standing.

Castiel sighed. "Goodnight, Dean.”

On his way back to his room, Dean passed his brother’s door and paused, running his hand through his short hair. He shook his head, sighed, and walked back towards it, rapping lightly. He heard a mumbled reply and opened the door.

“Dude, I said not now!” Sam was sitting on the end of his bed in sweatpants and a t-shirt, hastily wiping tears from his face.

Dean entered and closed the door. He opened his mouth but couldn’t find words. Instead, he walked towards him and placed a hand on his shoulder.

For Sam, the squeeze said what Dean was never eloquent enough to say. He hung his head. “This…this feels different than losing dad or Bobby or…”

“Or me?”

Sam nodded solemnly

“I know Sammy…he was a good kid. Hell, a great kid. And you were awesome with him.”

Sam’s face screwed up in grief and he put his face in his hands. Dean sat next to him on the bed and put an arm around him. Sam immediately wrapped his arms around him tightly. ‘He must have drank more than I thought,’ Dean wondered. They very rarely hugged; only when it was the end of the world or one of them came back from the dead. The sensation of Sam shaking from suppressed sobs caused Dean to close his eyes to stop his own tears from stinging. He squeezed his brother back and began feeling a sense of warmth and calm wash over him.

He felt his brother leaning into him now, seemingly exhausted. “I’ll let you get some rest.” He released his grip on Sam and stood. Sam hung his head again looking utterly despondent and drained from the day, the booze, and resisting tears. Dean was finding moving his feet impossible.

“Do you…should I….”

Sam raised his eyebrows and looked at him. “Suit yourself.”

Dean knew that if Sam didn’t want him to stay, he would have told him to fuck off by now. Cas was right; Sam needed his big brother.

“Get into bed," Dean said, taking his boots off.

Sam was too wiped to argue and obeyed. Dean sat on top of the comforter.

“You’re going to stay on top like a creep?”

“I thought you were too old for sleepovers Sammy.” Dean smiled and watched the gesture reflect on Sam’s face.

“Just until I fall asleep?” Sam repeated something he used to say to Dean when they were children.

Dean snorted laughter. He got under the covers in his flannel shirt and jeans. “Ok Sammy, until you fall asleep.”

Both men were on their backs looking up at the ceiling for some time.

“We should have done more," Sam finally said in almost a whisper.

“You know we tried everything we could," Dean said softly rolling onto his side to face his brother. His hand unconsciously found its way to Sam’s chest, giving it a rough rub.

Sam shook his head. “I should have tried harder.” His brow was set, voice getting stronger.

“You re-read every book in our library twice Sa-”

“I should have read them three times then,” Sam interjected sharply, running his hands through his hair, displacing Dean's hand with his elbow.

“Don’t do that." Dean’s face was full of steely concern; his brother was functioning on so little sleep and was at the end of his rope. He propped himself up on an elbow and turned Sam’s chin roughly to look at him. “This is not on you, man.”

“Don’t you fucking get it, I failed him!” Sam snapped pulling his face away from Dean’s hand, grabbing handfuls of flannel and giving him a shake.

“Sam…” Dean blinked, alarmed.

“No fuck you.” Sam tried to turn away from his brother but Dean pinned his shoulders

“Sam, you’re being an idiot," Dean growled gripping his shoulders hard and returned the shake.

Sam paused for a moment and shook the hair out of his eyes to look into his brother’s. “Fuck you," he repeated.

“Snap out of it.” Dean balled his fists in Sam’s t-shirt, exposing his stomach, and shoved him into the mattress.

Sam gasped after the air was pushed out of his lungs by his brother. “Do that again.”

Dean frowned harder. “Sam?”

“Push me.” Sam tightened his grip on Dean's soft flannel and shook him again.

“You’re starting to piss me off.” He pushed a knee between Sam’s legs for leverage and shoved Sam as hard as he could with both hands on his chest.

“Dean," Sam said with a slight moan. His big, clumsy hands reached and grabbed at Dean’s shirt, pulling his body down onto him, relishing the weight on his chest. “I need…I need to feel something different, anything.” A couple tears leaked from the corners of his eyes dampening the hair at his temples. He clung to the back of Dean’s shirt, painfully pinching Dean’s skin.

Dean pressed his forehead against Sam’s, feeling both of their hearts drumming quickly against his ribcage. He could feel Sam’s ragged breath on his lips and the desperation radiating off of him but felt confused. He placed a hand in Sam’s hair and gripped it experimentally.

Sam moaned softly pulling Dean’s shirt harder. Dean understood. His little brother needed what Dean was most apt at providing; harsh roughness, and he would do anything to take away Sam’s hurting.

He lifted his head and gripped a calloused hand around Sam’s jaw feeling his beard prick his fingers and palm. Sam arched underneath him, his darkening eyes pierced into Dean’s; silently spurring him on.

Dean slid his hand around Sam’s throat squeezing gently at first. One of Sam’s hands released Dean and gripped the hand around his neck, squeezing it tighter. Dean arched a brow and squeezed Sam tighter feeling his windpipe compress. As Sam emitted a low strangled moan, Dean felt the unmistakable pressure on his thigh of Sam’s hardening cock. He startled and dropped his hand, releasing Sam.

“ _Sammy…_ what-” Dean looked at him incredulously.

“Please don’t stop Dean…I need this…I can’t think anymore.” Sam unabashedly pressed his hips upwards into Dean’s thigh and pulled him down by his shirt so that their faces were close again. Dean groaned quietly against the tight fabric clinging to his neck; maybe he needed this too regardless of how fucked up in was.

“Sam it’s…I’m your broth-”

Sam lifted his head to press a firm kiss to his brother’s lips and Dean felt all sanity leave him. He brought his hand back into Sam’s hair, tangling his fingers in the strands and kissed him back hard. Years of closeness, years of losing each other, abandoning each other, searching, fearing the other getting harmed; this suddenly felt like the most sane and congruous thing they have ever done together.

Dean parted Sam’s lips with his tongue; his mouth tasted familiar and comforting. Sam’s hands were everywhere; clinging, grabbing, running over his muscular back. They finally they made their way under Dean’s shirt to roughly rub his skin, scraping him with his ragged, chewed fingertips. Dean shivered at his brother’s touch, groaning slightly at the sensation of Sam’s firm aggressive frame pressed against the bed.

“Take it off.” Sam broke the kiss, breathing heavily.

Dean slid the flannel off keeping his chest pressed against Sam’s. He felt Sam’s hands fisting and pulling up his t-shirt, He lifted up slightly to allow the shirt to be urgently wrenched off. He found Sam’s mouth again with his own, grasping his brother’s jaw again hard. Although they had barely started, Dean was enjoying bursts of pleasure and excitement within him and felt himself begin to get hard already.

Dean moved so that he could yank Sam up to hastily remove his shirt exposing his beautiful, toned torso. He shoved him back down, kissing him roughly, feeling their coarse chins grinding together. He bit his brother’s bottom lip causing Sam to moan and twist beneath him. Dean then forced Sam’s head to the side exposing his neck, biting down hard, tasting the salty skin between his teeth. Feeding off of Sam’s moaning and writhing, he continued to place bites along his neck, shoulder, clavicle, and chest leaving deeper and deeper indentations.

“Fuck yes, Dean.” One of Sam’s hands was gripping Dean’s hair as the other dug into his shoulder.

Dean rasped his tongue over Sam’s nipple feeling it harden along with his cock, now pressed against his abdomen. Dean bit down tentatively on the sensitive skin and Sam’s grasp tightened.

“Harder.”

Dean wrapped his hand around Sam’s ribcage and squeezed him to keep him still while he acquiesced. His brother’s guttural reaction made Dean grin around Sam’s skin. If this was what happened with his nipples, how would he react once he made it down to his, now throbbing, cock?

Dean continued his path, worshipping and abusing Sam’s skin until he licked a trail along the elastic of his sweatpants. He palmed Sam’s cock through the fabric, warming himself up to seeing it let alone putting it in his mouth. Sam’s stomach clenched and he moaned loudly. “D-Dean are you actually gunna…”

“Shhh Sammy…no thinking remember?” Dean growled quietly. He threw the covers onto the ground for more room, and focused his attention where Sam needed it. Taking a deep breath, he yanked his brother’s pants down over his hips and exposed his needy, engorged cock.

“Holy _fuck_ Sam,” Dean murmured, to which Sam grinned smugly. Dean slid to the end of the bed, grabbed Sam by the ankles, and dragged him so that his ass was on the edge. Dean pulled his pants off the rest of the way and kneeled between Sam’s legs, sliding his hands slowly, firmly up his thighs. Sam sat up and looked down at Dean biting his bottom lip.

Dean replaced his hands with his mouth, kissing and licking his skin, dragging his stubbled jaw closer and closer to Sam’s cock. Sam’s head tipped back; eyes pressed shut in anticipation. Dean took another deep breath choosing to take his own advice of not thinking, and licked a firm, wet line up the large vein in Sam’s dick. He then slipped the head in his mouth and sucked hard, gripping Sam’s thighs.

Sam groaned deeply and threw his hands on Dean again, as he took him fully into his mouth and sucked. Clamping down on Dean’s shoulders, Sam moaned his name and lifted his hips unconsciously, thrusting gently. Dean squeezed Sam’s thighs harder and sucked more aggressively, allowing Sam to fuck his mouth. When he sensed his little brother was close to finishing, he pulled away wiping the spit off his mouth and chin with the back of his hand.

Sam whined and laid back onto the bed, adjusting himself so that he was further back.

“Lube?” Dean rasped unbuckling his belt and undoing his fly.

“Bedside," Sam panted running his hands through his hair.

Dean found what he was looking for and threw it next to Sam. He pulled his jeans down followed by his precum-smeared boxers. His eyes were dark and full of lust for his brother.

Sam bit his lip again taking in his brother's naked, muscular body as Dean laid down next to him. Dean promptly grabbed the bottle, squirted some fluid on his fingers, and rubbed it on Sam’s hole causing Sam to whimper. Dean slid a finger inside of Sam, feeling his hot, tight ass clenching against him. Sam tipped his head down to seek out his brother’s mouth with his lips as Dean first slid his finger in and out and then added another. Once he was up to three fingers he spread and flexed them while Sam moaned wildly, cheek pressed against Dean’s forehead.

“I want you," Sam breathed as Dean bit into his shoulder again.

Dean pressed his eyes shut and growled low in the back of his throat. He fingered Sam more aggressively, moving his hips to press his own dripping cock against Sam’s thigh. Once he was as confident as he could be that Sam was ready, he centered himself between Sam’s legs, stroked lube on his cock, and nudged the tip of it against his brother’s ass. Sam moaned and glared at him. “Fucking do it.”

Dean pushed himself inside Sam gently breathing in deeply with the intense tightness of his brother’s ass. He hesitated; half of his cock buried inside Sam. “Sammy does it hurt?”

“I don’t care; fuck me.” His face was wincing but he hooked his heels around Dean’s upper thighs and pulled him forward so that his cock sunk deeper inside.

Dean moaned and immediately retracted his cock to slam back forward into Sam. Sam whined from the pain and pleasure, dragging his nails up Dean’s back. His eyes were blazing, pupils wide with desire. Dean began thrusting gently in and out of his brother, feeling Sam’s ass rippling around his cock, their chests pressed together.

“Sam are you- is it ok?” He panted searching Sam’s eyes, hand cupping his cheek. He had no idea whether Sam had ever done anal before.

“You feel fucking incredible, your cock is so big.” Sam’s head tipped back as the pain dissipated completely, pleasure flooding him.

“Oh my God Sammy…” He licked up Sam’s neck and bit his earlobe. He couldn’t believe how turned on it made him, hearing that from his brother.

“Harder Dean…fuck me harder.”

Dean obeyed, pulling his cock back and slamming forward, thrusting more urgently.

“Holy fuck I can’t believe this...” Sam rasped digging his fingers into Dean’s back. “ _Harder.”_

Dean sighed, feeling his dick throb from hearing the sound of Sam’s demanding tone and reveling in the sting from his brother’s hands. After giving him a rough deep kiss, he lifted himself off of Sam putting his weight back onto his knees and gripping Sam by his hips allowing for a deeper, more controlled thrust. He pressed his eyes shut feeling his cock fill Sam to it’s base. He began hammering into Sam, jostling him closer and closer to the headboard.

The sounds coming from Sam were obscene and were becoming louder with every punishing thrust Dean delivered. Dean thought the entire bunker filled with alternate universe soldiers must be able to hear him. He clamped a hand down on Sam’s mouth, pushing one of his long legs over his shoulder, to further angle into his brother. Sam’s eyes rolled back with pleasure as he struggled half-heartedly against Dean’s palm.

Dean bit his lip and grinned down at his younger brother, fucking him as hard as he could without giving him further brain damage. Sweat dripped off his forehead and chest, splattering Sam. “You like that, bitch? Hard enough for you?”

Sam glared at him with challenging, precocious eyes and shook his head vigorously. Dean raised his eyebrows “You little shit…” he moaned.

He pulled his cock out of Sam suddenly, causing Sam to arch violently, sending a muffled cry into Dean’s hand. Grabbing Sam’s waist and inner thigh, Dean dragged him to the edge of the bed and tossed him onto the covers on the floor, landing hard facing down. Dean got down on his knees running his hands roughly down Sam’s back, squeezing his ass hard to spread his cheeks enough to reveal his hole. “Get back inside of me _now_.” Sam growled rolling his hips.

Dean wasted no time burying his cock back into Sam’s inviting ass and immediately felt the difference of thrusting into him on the unforgiving floor. Sam nearly wailed with pleasure as Dean started brutally hammering him again. Sam was pressed firmly against the floor, Deans hands gripping and bruising his hips and ass.

Dean felt the pleasure mounting, his stomach clenching and balls tightening. “Sammy...I-”

“Come in me Dean," Sam hissed.

Dean groaned and slid a hand around Sam’s throat squeezing hard. Sam unexpectedly came violently, dousing the covers underneath him, lifting his hips into his brother’s rigid cock as pleasure pulsed through him.

Feeling Sam’s hot insides clench aggressively around him pushed Dean over the edge, filling his ass with come. He collapsed on top of Sam, releasing his throat, torso sliding in the joined sweat. “Jesus Christ," he murmured, " I ca-can’t believe you came without me t-touching your dick," he stuttered as aftershocks ran through him.

“Fuck, me either," Sam panted, smiling softly and closing his eyes, appreciating his brother’s weight as Dean brushed his wet hair off his face and neck. Eventually, as their hearts steadied and their breathing returned to normal, Dean pulled his softened dick out of Sam and rolled off of him onto his back, wiping the sweat from his face. When Dean went to sit up, Sam grabbed at his shoulders weakly, indicating for him to stay. That night, Dean fell asleep on the floor with his little brother curled against his chest, finally getting the rest he needed.

* * *

Dean awoke alone on the floor feeling stiff, hung over, and filthy with dried sweat and come.

“Sammy?” He called into the room with no reply.

He sat up and clutched his head looking around for his discarded clothes. Once he was up and dressed, he shuffled painfully out of the room following the sound of voices coming from the war room.

“Do you think it’s possible?” He heard Castiel say.

“I think so, maybe.” An unknown woman’s voice spoke.

“Maybe what?” Dean grunted entering the room. His looked at his brother and met his eyes, exchanging a smile. Sam looked relaxed, rested, and had the familiar, hopeful, I-have-a-plan look about him. The only thing that tore Dean’s focus away in that moment was the strange, eye-patched, woman saying his name.

“Hello, Dean," Lily said.


End file.
